Excited live trivia host in front of a laptop

Think you have what it takes to run the show? Then we want to talk to YOU!

We’re Seeking Dynamic Personalities to Grow Our Family Brand

Challenge Entertainment is always looking for entertaining people with great attitudes and fun personalities to host our weekly venues. If you are 18 years of age or older, have great stage presence and can entertain a crowd, then becoming a Challenge Entertainment Trivia Jockey might be the right fit for you!

Joining Challenge Entertainment as a Trivia Jockey can provide an excellent source of supplemental income featuring competitive pay, flexible hours and the most fun you will ever have and still be able to call it work.

You Don’t Have to be a Trivia Genius to Host One of Our Shows!

We’ll train you and give you step-by-step guidelines on how to run a show, teach you the rules of the game and even give you tips on how to keep the audience engaged.

What we’ll need from you is commitment, dependability, punctuality and professionalism. Remember, you’re representing the Challenge Entertainment brand and we’re considered one of the best in the biz because of the awesome people we hire.

We will require that you provide your own form of reliable transportation to get you to and from the shows and you’ll need your own laptop computer and an active cell phone so we can stay in touch. Shows are typically 2 to 3 hours on Monday through Thursday and start anywhere from 6 to 10 PM.

A team playing pub trivia

Who’s a Good Fit to be a Trivia Jockey?

Smiling woman in front of a professional microphone


Many of our hosts have a background in theater, radio, podcasts, communications or public speaking. Experience in front of an audience is a huge plus!

Two women pointing and having fun in a bar


Both part-time and full-time students love the flexibility of being a Challenge Entertainment Trivia Jockey. Regular shows help you set your schedule according to your needs.

A male bartender with his hand on a beer tap and passing a pint to a customer

Servers and Bartenders

We see you working hard out there! You know the patrons and the business, now it’s time to show your skills behind the mic!

What Our Jockeys Say ...

Being a trivia jockey is being the life of the party, which is why I love it. I've hosted crowds larger than most local bands will ever play to. You get to create the atmosphere, entertain the crowd, and provide a fun and interactive experience. I just love being able to turn an otherwise dull Monday night into something that both my crowd and I look forward to every week.

- Tyler Banks, Trivia Jockey

Amazing Company
Great fun time. Hosting shows is the best. The opportunity to advance is very present. There is so much you can do with them if you have the drive to get it all done. They just need someone to take the initiative and grow the company.

- Trivia Jockey, Biloxi MS, Posted on Indeed.com

Super Fun Side Job
If you enjoy trivia, hanging out at bars, meeting new people, and entertaining people, this is a great gig. All you have to so I set up your equipment, read the questions the company sends to you, play some music, and keep score. I thoroughly enjoy and look forward to every show.

- Trivia Jockey, Pembroke Pines FL, Posted on Indeed.com